Organic photochromic compositions of improved kinetic performance

ABSTRACT

Described are imbibition compositions that incorporate kinetic enhancing additive(s) into photochromic polymeric host material. Kinetic enhancing additives include organic polyol(s), epoxy-containing compound(s) or a mixture thereof that improves the performance of organic photochromic compounds in the polymeric host as determined in the Photochromic Performance Test. Also described is a process for incorporating kinetic enhancing additives into polymeric substrates prior to, after and/or with organic photochromic compounds and the resulting photochromic articles produced by such a process.

CROSS REFERENCE TO RELATED APPLICATIONS

[0001] This Application is a Continuation-In-Part of application Ser.No. 09/724,145 filed Nov. 28, 2000, which application is incorporatedherein by reference.

DESCRIPTION OF THE INVENTION

[0002] The present invention relates to photochromic compositions ofenhanced kinetic performance and to a method for improving theperformance of organic photochromic compounds in polymeric substrates.More particularly, this invention relates to compositions comprisingkinetic enhancing additive(s) (KEA) and organic photochromiccompound(s), and optionally, carrier, stabilizer and/or conventionaladditive(s). The KEA is used in an amount sufficient to improve theperformance of organic photochromic compounds in polymeric organic hostmaterials, e.g., polymerizates and polymeric coatings. The KEA(s) may betransferred prior to, after or with the photochromic compound(s) or in acombination of such steps. Still more particularly, this inventionrelates to photochromic articles, e.g., ophthalmic lenses, made ofpolymeric substrates having incorporated therein organic photochromiccompounds and KEA(s) such as epoxy-containing compound(s), organicpolyols and/or a mixture thereof.

[0003] Photochromic compounds exhibit a reversible change in color whenexposed to radiation including ultraviolet rays, such as the ultravioletradiation in sunlight or the light of a mercury lamp. Various classes ofphotochromic compounds have been synthesized and suggested for use inapplications in which a sunlight-induced reversible color change ordarkening is desired. The most widely described classes are oxazines,chromenes and fulgides.

[0004] Photochromic compounds may be incorporated into plasticsubstrates, such as ophthalmic lenses, by various methods described inthe art. Such methods include dissolving or dispersing the compoundwithin the surface of a substrate, e.g., imbibition of the photochromiccompound into the substrate by immersion of the substrate in a hotsolution of the photochromic compound or by depositing the photochromiccompound on the surface of the substrate and thermally transferring thephotochromic compound into the substrate. The term “imbibition” or“imbibe” is intended to mean and include permeation of the photochromiccompound into the substrate, solvent assisted transfer absorption of thephotochromic compound into the substrate, vapor phase transfer and othersuch transfer mechanisms.

[0005] The extent to which the photochromic compounds penetrate thepolymeric substrate generally increases with increasing temperature,increasing concentration of photochromic compounds at the surface of thepolymeric substrate and increasing period of contact with the polymericsubstrate. The ease with which the photochromic compounds areincorporated is also dependent upon the characteristics of thephotochromic compounds and of the polymeric substrate. The molecularsize, melting point and solvent solubility of the photochromic compoundsas well as the receptivity of the polymeric substrate all affect theease of incorporation of the photochromic compounds. Due to the numerousvariables affecting production of photochromic articles, in some cases,photochromic compounds may not be incorporated into the plasticsubstrate with sufficient uniformity and to a sufficient depth. This canresult in poor performance of the photochromic compound and inadequatereversible color change of the photochromic article.

[0006] Methods for incorporating photochromic compounds into polymericsubstrates have been disclosed in U.S. Pat. Nos. 4,286,957, 4,880,667,5,789,015, 5,914,193 and 5,975,696. Various photochromic compositionsused in the process of incorporating photochromic compounds intopolymeric substrates have been disclosed in U.S. Pat. Nos. 5,185,390,5,391,327 and 5,770,115.

[0007] The aforementioned photochromic compositions and methods ofincorporating photochromic compounds into polymeric substrates aregenerally known in the art and can be used in the process of the presentinvention.

[0008] The use of epoxy-containing compounds with photochromic compoundshas been disclosed in U.S. Pat. Nos. 5,395,566, 5,462,698, 5,621,017 and5,776,376. U.S. Pat. No. 5,395,566 discloses a photochromic compositionof a compound having at least one radical polymerizable group and atleast one epoxy group and a photochromic compound. U.S. Pat. No.5,462,698 discloses a photochromic composition of a compound having atleast one epoxy group, a fulgide compound and two different(meth)acrylic monomers. U.S. Pat. No. 5,621,017 discloses a photochromiccomposition of a radical polymerization monomer, photochromic compoundand photopolymerization initiator. U.S. Pat. No. 5,776,376 discloses aphotochromic composition of a polymerizable monomer composed of acompound having at least one epoxy group, various monomers, anα-methylstyrene dimer and photochromic compounds.

[0009] In each of the aforedescribed patents disclosing compositionscontaining epoxy-containing compounds and photochromic compounds, thecompositions contained radically polymerizable components and werepolymerized to make photochromic lenses.

[0010] Although methods exist for incorporating photochromic compoundsinto polymeric substrates, improvements in such methods are sought. Ithas now been discovered that transferring a photochromic performanceimproving amount of kinetic-enhancing additives and a photochromicamount of photochromic compound into an organic polymeric host willresult in improved performance of a photochromic compound in thePhotochromic Performance Test described in Example 25. This improvementin performance is demonstrated when the photochromic compound(s) istransferred simultaneously with the KEA, prior to the KEA, after the KEAor by using a combination of such steps.

[0011] In one contemplated embodiment, the KEA is included in aremovable imbibition composition containing organic photochromiccompound(s), and that optionally includes carrier, light stabilizer(s),ultraviolet light absorber(s), antioxidant(s), rheology controlagents(s) and/or leveling agent(s). Photochromic articles demonstratingimproved photochromic performance may be produced by the process of thepresent invention.

DETAILED DESCRIPTION OF THE INVENTION

[0012] In accordance with the present invention, a KEA is defined hereinas a material which when transferred into a polymeric host withphotochromic compound(s), prior to the photochromic compounds, after thephotochromic compounds or by a combination of at least two of suchsteps, results in an increased rating in the Photochromic PerformanceTest described in Example 25. The ratings of the test are defined as theresult obtained when the change in optical density (ΔOD) at 15 minutesis divided by the Bleach (T ½) and then multiplied by 10,000.

[0013] A photochromic performance improving amount of the KEA is definedherein as the amount necessary to transfer into a organic polymeric hostto result in an increased rating in the Photochromic Performance Test ascompared to a organic polymeric host substantially free of the KEA. Thisamount may be transferred into the polymeric host all at once or byfirst transferring a portion of the amount in one step followed by theremainder of the amount in one or more subsequent transfer steps priorto, after or with the transfer of a photochromic amount of photochromiccompound(s). Materials which are KEA(s) include, but are not limited to,organic polyols, epoxy-containing compound(s) and mixtures thereof.

[0014] Other than in the operating examples, or where otherwiseindicated, all numbers expressing quantities of ingredients or reactionconditions used herein are to be understood as modified in all instancesby the term “about”.

[0015] The disclosures of the patents and articles cited herein relatedto photochromic compounds, lactone polyesters, stabilizers,poly(urea-urethanes), polymeric organic host materials, photochromiccompositions, i.e., photochromic imbibition compositions, methods ofincorporating photochromic compounds into a polymeric substrate andmethods for producing hard or soft contact lenses are incorporatedherein, in toto, by reference.

[0016] In each instance where the term “weight percent” is used hereinwith respect to the imbibition composition, it is to be understood thatthe described weight percent is based on the total weight of theimbibition composition.

[0017] Organic polyols are polyhrdric alcohols having 2 or more hydroxylgroups. The organic polyols that may be used in the present inventioninclude (a) polyester polyols; (b) polyether polyols; (c)amide-containing polyols; (d) polyhydric polyvinyl alcohols; and (e)mixtures of such polyols. In one contemplated embodiment, the organicpolyols are selected from polyether polyols, polyester polyols ormixtures thereof. In another contemplated embodiment, the organicpolyols are selected from polycaprolactone diol, poly(ethylene glycol),hexane diol, polytetrahydrofuran diol or a mixture thereof.

[0018] Polyester polyols are generally known. They are prepared byconventional techniques utilizing low molecular weight diols, triols andpolyhydric alcohols known in the art (optionally in combination withmonhydric alcohols) with polycarboxylic acids. Examples of such lowmolecular weight polyols include ethylene glycol, trimethylolpropane andpentaerythritol. Examples of suitable polycarboxylic acids include:phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid,tetrahydrophthalic acid, adipic acid, succinic acid, glutaric acid,fumaric acid and mixtures thereof. Anhydrides of the above acids, wherethey exist, can also be employed and are encompassed by the term“polycarboxylic acid”. If a triol or polyhydric alcohol is used, amonocarboxylic acid, such as acetic acid and/or benzoic acid, may beused in the preparation of the polyester polyols, and for some purposes,such a polyester polyol maybe desirable.

[0019] Moreover, polyester polyols are understood herein to includepolyester polyols modified with fatty acids or glyceride oils of fattyacids (i.e., conventional alkyd polyols containing such modification).In addition, certain materials that react in a manner similar to acidsto form polyester polyols are also useful. Such materials includelactones, e.g., caprolactone, propiolactone and butyrolactone, andhydroxy acids such as hydroxycaproic acid and dimethylol propionic acid.Lactone polyesters are described in U.S. Pat. No. 3,169,945.Commercially available lactone polyesters or polycaprolactone polyolsare sold under the trademarks PLACCEL (Daicell Co. Ltd.) and TONE (UnionCarbide).

[0020] In one embodiment when the polyester polyol is represented by thefollowing formula:

R₆—(X—(C(O)(—CR₇R₈)_(h)—CHR₉—O)_(t)—H)_(y)

[0021] wherein:

[0022] X is —O— or —NR₁₀— and R₁₀ is hydrogen or C₁ -C₁₂ alkyl; R₆ is anorganic radical derived from an initiator. Initiators are compoundshaving at least one reactive hydrogen capable, with or without the aidof a catalyst, of opening the lactone ring and adding it as an openchain without forming water of condensation. Initiators includemonofunctional initiators such as alcohols and amines, andpolyfunctional initiators such as polyols, polyamines, aminoalcohols,and vinyl polymers, as well as amides, sulfonamides, hydrozones,semicarbazones, oximes, polycarboxylic acids, hydroxy carboxylic acidsand amino-carboxylic acids. R₇, R₈ and R₉ are each selectedindependently from hydrogen, C₁ -C₁₂ alkyl, C₅-C₆ cycloalkyl, C₁ -C₆alkoxy, benzyl or phenyl, provided that at least h+2 of the total numberof R₇, R₈ and R₉ are hydrogen. For example, when butyrolactone (C₄H₆O₂)is the starting material, h is 2 and at least 4, actually 5 of the totalnumber of R₇, R₈ and R₉ are hydrogen. The letter h is an integer from 1to 6; t is an integer from 1 to 100; and y is an integer equal to from 2to 6.

[0023] In another contemplated embodiment, the polyester polyol is thereaction product of a diol initiator and a lactone, i.e., a polylactonediol. The diol of the polylactone diol may be selected from linear orbranched aliphatic diols having from 2 to 20 carbon atoms,poly(C₂-C₄)alkylene glycols, cycloaliphatic diols having from 5 to 8carbon atoms in the cyclic ring, monocyclic aromatic diols, bisphenols,hydrogenated bisphenols and mixtures thereof.

[0024] Examples of linear or branched aliphatic diols having from 2 to20 carbon atoms that may be used to prepare the polylactone diol includebut are not limited to, ethylene glycol, propylene glycol, 1,3-propanediol, 1,2- and 2,3-butane diol, pentane diols, hexane diols, heptanediols, octane diols, nonane diols, decane diols, undecane diols,dodecane diols, tridecane diols, tetradecane diols, pendadecane diols,hexadecane diols, hetadecane diols, octadecane diols, nonadecane diolsand icosane diols. Examples of poly(C₂-C₄)alkylene glycols include, butare not limited to, di-, tri-, tetra-, penta- and higher ethyleneglycols, di-, tri-, tetra-, penta- and higher propylene glycols, anddi-, tri-, tetra-, penta- and higher butylene glycols.

[0025] Cycloaliphatic diols having from 5 to 8 carbon atoms that may beused to prepare the polylactone diol include, but are not limited to,those cycloaliphatic diols described previously herein, and cyclopentanediol, cyclohexane diol, cyclohexane dimethanol, cycloheptane diol andcyclooctane diol. Examples of monocyclic aromatic diols that may be usedto prepare the polylactone diol include but are not limited to, benzenediol, e.g., 1,2-dihydroxy benzene and 1,3-dihydroxy benzene; C₁ -C₄alkyl substituted benzene diol, e.g., 4-tert-butyl-benzene-1,2-diol,4-methyl-benzene-1,2-diol, 3-tert-butyl-5-methyl-benzene-1,2-diol and3,4,5,6-tetramethyl-benzene-1,2-diol; halo substituted benzene diol,e.g., 3,5-dichlorobenzene-1,2-diol, 3,4,5,6-tetrabromo-benzene-1,2-dioland 3,4,5-trichloro-benzene-1,2-diol; and C₁-C₄ alkyl and halosubstituted benzene diol, e.g., 3-bromo-5-tert-butyl-benzene-1,2-diol,3,6-dichloro-4-methyl-benzene-1,2-diol,3,-bromo-4,5-dimethyl-benzene-1,2-diol and3-chloro-4,6-di-tert-butyl-benzene-1,2-diol.

[0026] Bisphenols and hydrogenated bisphenols that may be used toprepare the polylactone diol may be represented by the followingformula:

[0027] wherein R₁₁ and R₁₂ are each selected independently from eachother for each f and g from C₁-C₄ alkyl, chlorine and bromine; f and gare each independently an integer from 0 to 4; and —J— is a divalentlinking group selected from —O—, —S—, —S(O₂)—, —C(O)—, —CH₂—,—CH═CH—,—C(CH₃)₂—, —C(CH₃)(C₆H₅)— and

[0028] represents a benzene ring or a cyclohexane ring. An example of abisphenol that may be used to prepare the polylactone diol is4,4′-isopropylidenebisphenol. An example of a hydrogenated bisphenolthat may be used to prepare the polylactone diol is4,4′-isopropylidenebiscyclohexanol.

[0029] The lactone used to prepare the polylactone diol has from 3 to 8carbon atoms in the cyclic lactone ring and may be represented by thefollowing formula,

[0030] wherein h is an integer from 1 to 6, e.g., 1, 2, 3, 4, 5 or 6,R₇, R₈ and R₉ are each selected independently from hydrogen, C₁-C₁₂alkyl, C₅-C₆ cycloalkyl, C₁-C₆ alkoxy, benzyl and phenyl, provided thatat least h+2 of the total number of R₇, R₈ and R₉ groups are hydrogen.Typically R₇, R₈ and R₉ are each hydrogen.

[0031] Examples of lactones that may be used to prepare the polylactonediol include, but are not limited to: beta-propiolactone;gamma-butyrolactone; beta-butyrolactone; delta-valerolactone;alpha-methyl-gamma-butyrolactone; beta-methyl-gamma-butyrolactone;gamma-valerolactone; epsilon-caprolactone; monomethyl-, monoethyl-,monopropyl-, monoisopropyl- etc. through monododecylepsilon-caprolactones; methoxy and ethoxy epsilon-caprolactones;cyclohexyl epsilon-caprolactones; phenyl epsilon-caprolactones; benzylepsilon-caprolactones; zeta-enatholactone; and eta-caprylactone. In apreferred embodiment of the present invention, R₇, R₈ and R₉ are eachhydrogen, h is 4 and the lactone is epsilon-caprolactone.

[0032] Polyether polyols are generally known. Examples of polyetherpolyols include various polyoxyalkylene polyols, polyalkoxylatedpolyols, e.g., poly(oxytetramethylene)diols, and mixtures thereof. Thepolyoxyalkylene polyols can be prepared, according to well-knownmethods, by condensing alkylene oxide, or a mixture of alkylene oxideusing acid or base catalyzed addition, with a polyhydric initiator or amixture of polyhydric initiators such as ethylene glycol, propyleneglycol, glycerol, sorbitol and the like. Illustrative alkylene oxidesinclude ethylene oxide, propylene oxide, butylene oxide, amylene oxide,aralkylene oxides, e.g., styrene oxide, and the halogenated alkyleneoxides such as trichlorobutylene oxide and so forth. The more preferredalkylene oxides include propylene oxide and ethylene oxide or a mixturethereof using random or step-wise oxyalkylation. Examples of suchpolyoxyalkylene polyols include polyoxyethylene, i.e., polyethyleneglycol, polyoxypropylene, i.e., polypropylene glycol.

[0033] Polyalkoxylated polyols may be represented by the followinggraphic formula V,

[0034] wherein a and b are each a positive number, the sum of a and bbeing from 2 to 70, R₄ and R₅ are each hydrogen, methyl or ethyl,preferably hydrogen or methyl and D is a divalent linking group selectedfrom straight or branched chain alkylene (usually containing from 1 to 8carbon atoms), phenylene, C₁-C₉ alkyl substituted phenylene or a grouprepresented by the aforementioned graphic formula IV. Such materials maybe prepared by methods that are well known in the art. One such commonlyused method involves reacting a polyol, e.g.,4,4′-isopropylidenediphenol, with an oxirane containing substance, forexample ethylene oxide, propylene oxide, α-butylene oxide or β-butyleneoxide, to form what is commonly referred to as an ethoxylated,propoxylated or butoxylated polyol having hydroxy functionality.

[0035] Examples of polyols suitable for use in preparing thepolyalkoxylated polyols include low molecular weight polyols; phenylenediols such as ortho, meta and para dihydroxy benzene; alkyl substitutedphenylene diols such as 2,6-dihydroxytoluene, 3-methylcatechol,4-methylcatechol, 2-hydroxybenzyl alcohol, 3-hydroxybenzyl alcohol, and4-hydroxybenzyl alcohol; dihydroxybiphenyls such as4,4′-dihydroxybiphenyl and 2,2′-dihydroxybiphenyl; bisphenols such as4,4′-isopropylidenediphenol; 4,4′-oxybisphenol;4,4′-dihydroxybenzenephenone; 4,4′-thiobisphenol; phenolphthalein;bis(4-hydroxyphenyl)methane; 4,4′-(1,2-ethenediyl)bisphenol; and4,4′-sulfonylbisphenol; halogenated bisphenols such as4,4′-isopropylidenebis(2,6-dibromophenol),4,4′-isopropylidenebis(2,6-dichlorophenol) and4,4′-isopropylidenebis(2,3,5,6-tetrachlorophenol); and biscyclohexanols,which can be prepared by hydrogenating the corresponding bisphenols,such as 4,4′-isopropylidene-biscyclohexanol; 4,4′-oxybiscyclohexanol;4,4′-thiobiscyclohexanol; and bis(4-hydroxycyclohexanol)methane.

[0036] The polyether polyols also include the generally knownpoly(oxytetramethylene)diols or polytetrahydrofuran diols prepared bythe polymerization of tetrahydrofuran in the presence of Lewis acidcatalysts such as boron trifluoride, tin (IV) chloride and sulfonylchloride.

[0037] In one contemplated embodiment, the polyether polyols areselected from the group polyoxyalkylene polyols, polyalkoxylatedpolyols, poly(oxytetramethylene)diols or mixtures thereof.

[0038] Amide-containing polyols are generally known and typically areprepared from the reaction of diacids or lactones and low molecularweight polyols, e.g., aliphatic diols, triols, etc., with diamines oraminoalcohols as described hereinafter. For example, amide-containingpolyols may be prepared by the reaction of neopentyl glycol, adipic acidand hexamethylenediamine. The amide-containing polyols may also beprepared through aminolysis by the reaction, for example, ofcarboxylates, carboxylic acids, or lactones with amino alcohols.Examples of suitable diamines and amino alcohols includehexamethylenediamines, ethylenediamines, phenylenediamine,monoethanolamine, diethanolamine, isophorone diamine and the like.

[0039] Polyhydric polyvinyl alcohols are generally known and can beprepared, for example, by the polymerization of vinyl acetate in thepresence of suitable initiators followed by hydrolysis of at least aportion of the acetate moieties. In the hydrolysis process, hydroxylgroups are formed which are attached directly to the polymer backbone.In addition to homopolymers, copolymers of vinyl acetate and monomerssuch as vinyl chloride can be prepared and hydrolyzed in similar fashionto form polyhydric polyvinyl alcohol-polyvinyl chloride copolymers.

[0040] Epoxy-containing compounds that may be used in the practice ofthe present invention may be selected from the compounds represented bythe following graphic formulae I, II, III or a mixture thereof.

[0041] In graphic formulae I, II and III, R₁ is hydrogen or C₁ -C₃alkyl. Letter n is an integer selected from one, two, three or four.When n is equal to one in graphic formula I, A is selected from C₂-C₂₀alkyl, substituted C₂-C₂₀ alkyl, C₃-C₂₀ cycloalkyl, substituted C₃-C₂₀cycloalkyl; the unsubstituted or substituted aryl groups, phenyl andnaphthyl; aryl(C₁ -C₃)alkyl, substituted aryl(C₁ -C₃)alkyl, acryloxy,methacryloxy; the group —C(O)Y, wherein Y is C₂-C₂₀ alkyl, C₁ -C₆ alkoxyor aryl; or the group —R—(OR)_(m)—OH or —(OR)_(m)—OH wherein R is C₂-C₄alkylene and m is an integer from 1 to 20. The substituents of the alkyland cycloalkyl groups are carboxy, hydroxy and/or C₁-C₃ alkoxy. Thesubstituents of the aryl and aryl(C₁-C₃)alkyl groups are carboxy,hydroxy, C₁ -C₃ alkoxy and/or C₁ -C₃ alkyl. When n is from two to four,A is selected from C₂-C₂₀ alkylene, substituted C₂-C₂₀ alkylene, C₃-C₂₀cycloalkylene, substituted C₃-C₂₀ cycloalkylene; the unsubstituted orsubstituted arylene groups, phenylene and naphthylene; aryl(C₁-C₃)alkylene, substituted aryl(C₁-C₃)alkylene; the group —C(O)Z(O)C—,wherein Z is C₂-C₂₀ alkylene or arylene; the group —R—(OR)_(m)— or—(OR)_(m)—, wherein R and m are the same as defined hereinbefore;phthaloyl, isophthathoyl, terephthaloyl, hydroxyl-substituted phthaloyl,hydroxy-substituted isophthaloyl, hydroxy-substituted terephthaloyl; ora group represented by the following graphic formula IV:

[0042] wherein R₂ and R₃ are each C₁ -C₄ alkyl, chlorine or bromine; pand q are each an integer from 0 to 4;

[0043] represents a divalent benzene group or a divalent cyclohexanegroup; G is —O—, —S—, —S(O₂)—, —C(O)—, —CH₂—, —CH═CH—,—C(CH₃)₂—,—C(CH₃)(C₆H₅)—, —(C₆H₄)— or

[0044] when

[0045] is the divalent benzene group; or G is —O—, —S—, —CH₂—, or—C(CH₃)₂—, when

[0046] is the divalent cyclohexane group. The substituents of thealkylene and cycloalkylene groups are carboxy, hydroxy and/or C₁-C₃alkoxy. The substituents of the aryl and aryl(C₁-C₃)alkylene groups arecarboxy, hydroxy, C₁ -C₃ alkoxy and/or C₁ -C₃ alkyl.

[0047] In graphic formulae II and III, B is selected from C₂-C₂₀ alkyl,substituted C₂-C₂₀ alkyl, C₃-C₂₀ cycloalkyl, substituted C₃-C₂₀cycloalkyl; the unsubstituted or substituted aryl groups, phenyl andnaphthyl; aryl(C₁-C₃)alkyl or substituted aryl(C₁ -C₃)alkyl. The alkyland cycloalkyl substituent are carboxy, hydroxy and/or C₁ -C₃ alkoxy.The aryl and aryl(C₁-C₃) substituents are carboxy, hydroxy, C₁ -C₃alkoxy and/or C₁ -C₃ alkyl. In one contemplated embodiment, R₁ ishydrogen or methyl. When n is one, A is selected from C₂-C₂₀ alkyl,hydroxyl-substituted C₂-C₂₀ alkyl, C₃-C₂₀ cycloalkyl,hydroxyl-substituted C₃-C₂₀ cycloalkyl, phenyl, naphthyl,aryl(C₁-C₃)alkyl; the group —C(O)Y, wherein Y is C₂-C₂₀ alkyl, C₁ -C₆alkoxy or aryl; the group —R—(OR)_(m)—OH or —(OR)_(m)—OH, wherein R isC₂-C₄ alkylene and m is an integer from 1 to 20; acryloxy ormethacryloxy. When n is from two to four, A is selected from C₂-C₂₀alkylene, hydroxyl-substituted C₂-C₂₀ alkylene, C₃-C₂₀ cycloalkylene,phenylene, naphthylene, aryl(C₁ -C₃)alkylene; the groups —R—(OR)_(m)— or—(OR)_(m)—, wherein R and m are the same as defined hereinbefore;phthaloyl, isophthathoyl, terephthaloyl, or a group represented bygraphic formula IV wherein R₂ and R₃ are each C₁-C₄ alkyl, chlorine orbromine; p and q are each an integer from 0 to 4;

[0048] represents a divalent benzene group or a divalent cyclohexanegroup; G is —O—, —C(O)—, —CH₂—, or —(C₆H₄)— when

[0049] is the divalent benzene group, or G is —O— or —CH₂—, when

[0050] is the divalent cyclohexane group.

[0051] B is selected from C₂-C₂₀ alkyl, C₃-C₂₀ cycloalkyl; theunsubstituted and hydroxyl-substituted aryl groups, phenyl and naphthyl;or aryl(C₁-C₃)alkyl.

[0052] In another contemplated embodiment, R₁ is hydrogen. When n isone, A is selected from C₂-C₁₀ alkyl, phenyl, the group —R—(OR)_(m)—OH,or —(OR)_(m)—OH, wherein R is C₂-C₄ alkylene and m is an integer from 1to 20. When n is from two to four, A is selected from C₂-C₁₀ alkylene,phenylene, the group —R—(OR)_(m)— or —(OR)_(m)—, wherein R and m are thesame as defined hereinbefore; and phthaloyl. B is selected from C₂-C₁₀alkyl, phenyl or phenyl(C₁-C₃)alkyl.

[0053] Examples of the compound having at least one epoxy group in themolecule include ethylene glycol glycidyl ether, propylene glycolglycidyl ether, glycerol polyglycidyl ether, diglycerol polyglcidylether, glycerol propoxylate triglycidyl ether, trimethylolpropanetriglycidyl ether, sorbitol polyglycidyl ether, butyl glycidyl ether,phenyl glycidyl ether, poly(ethylene glycol)diglycidyl ether,poly(propylene glycol)diglycidyl ether, neopentyl glycol diglycidylether, N,N-diglycidyl-4-glycidyloxyaniline, glycidyl phthalimide,N,N-diglycidyl toluidine, 1,6-hexane diol diglycidyl ether, diglycidyl1,2-cyclohexanedicarboxylate, bisphenol A or hydrogenated bisphenol Apropylene oxide adduct, diglycidyl ester of terephthalic acid,diglycidyl 1,2,3,6-tetrahydrophthalate, spiroglycol diglycidyl ether andhydroquinone diglycidyl ether. Such compounds may be used individuallyor in combination as mixtures.

[0054] The combination of organic polyols and epoxy-containing compoundsfor use in the transfer process or in the removable imbibitioncomposition may be in a weight proportion of from 1:99 to 99:1; 5:95 to95:5; 10:90 to 90:10; 50:50 or in a proportion between any of thesevalues, inclusive of the recited ratios, e.g., from 30:70 to 60:40.

[0055] The amount of KEA used in the removable imbibition composition isnot critical provided that it is a photochromic performance improvingamount. Such an amount may range from 0.1 to 99.9 weight percent of theimbibition composition. In one contemplated embodiment, the amount ofKEA ranges from 1 to 75 weight percent of the imbibition composition. Inanother contemplated embodiment, the amount of KEA ranges from 2 to 50weight percent. In a still further contemplated embodiment, the amountof KEA ranges from 3 to 30 weight percent. The amount of KEA used mayrange between any combination of these values, inclusive of the recitedranges, e.g., from 0.15 to 99.85 weight percent, provided that theamount used is a photochromic performance improving amount.

[0056] The improvement in the photochromic performance resulting fromthe addition of the KEA to the imbibition composition is evident by ahigher rating in the Photochromic Performance Test than that of acomposition without the KEA. The percent improvement can be determinedby subtracting the rating of the composition without KEA from the ratingof the composition with the KEA, dividing the result by the rating ofthe composition without KEA and multiplying by 100. The higher thepercent improvement, the greater the effect of the KEA and the moredesirable the result. For example, percent improvements of 10, 15, 20,30, 50, 90, 100, 200, 500, 1000, 1500 and higher are more desirable thanpercent improvements of from 1 to less than 10.

[0057] The photochromic compounds used in the photochromic compositionof the present invention may be used alone or in combination with one ofmore other appropriate complementary organic photochromic compounds,i.e., organic photochromic compounds having at least one activatedabsorption maxima within the range of 400 and 700 nanometers, and whichcolor when activated to an appropriate hue.

[0058] The complementary organic photochromic compounds may includepolymerizable photochromic compounds, such as those disclosed in U.S.Pat. Nos. 4,719,296; 5,166,345; 5,236,958; 5,252,742; 5,359,085; and5,488,119. Further examples of complementary organic photochromiccompounds include naphthopyrans, e.g., naphtho[1,2-b]pyrans andnaphtho[2,1-b]pyrans, quinopyrans, indenonaphthopyrans, oxazines, e.g.,benzoxazines, naphthoxazines and spiro(indoline)pyridobenzoxazines,phenanthropyrans, e.g., substituted 2H-phenanthro[4,3-b]pyran and3H-phenanthro[1,2-b]pyran compounds, benzopyrans, e.g., benzopyrancompounds having substituents at the 2-position of the pyran ring, andmixtures of such photochromic compounds. Such photochromic compounds aredescribed in U.S. Pat. Nos. 3,562,172; 3,567,605; 3,578,602; 4,215,010;4,342,668; 4,816,584; 4,818,096; 4,826,977; 4,880,667; 4,931,219;5,066,818; 5,238,981; 5,274,132; 5,384,077; 5,405,958; 5,429,774;5,458,814, 5,466,398; 5,514,817; 5,552,090; 5,552,091; 5,565,147;5,573,712; 5,578,252; 5,637,262; 5,645,767; 5,656,206; 5,658,500;5,658,501; 5,674,432 and 5,698,141. Spiro(indoline)pyrans are alsodescribed in the text, Techniques in Chemistry, Volume III,“Photochromism”, Chapter 3, Glenn H. Brown, Editor, John Wiley and Sons,Inc., New York, 1971.

[0059] Other complementary photochromic substances contemplated aremetal-dithiozonates, e.g., mercury dithizonates which are described in,for example, U.S. Pat. No. 3,361,706; and fulgides and fulgimides, e.g.,the 3-furyl and 3-thienyl fulgides and fulgimides, which are describedin U.S. Pat. No. 4,931,220 at column 20, line 5 through column 21, line38.

[0060] The photochromic articles of the present invention may containone photochromic compound or a mixture of photochromic compounds, asdesired.

[0061] Each of the photochromic substances described herein may be usedin amounts (or in a ratio) such that a polymeric substrate to which thephotochromic composition is associated, exhibits a desired resultantcolor, e.g., a substantially neutral color when activated withunfiltered sunlight, i.e., as near a neutral color as possible given thecolors of the activated photochromic compounds. Neutral gray and neutralbrown colors are preferred. Further discussion of neutral colors andways to describe colors may be found in U.S. Pat. No. 5,645,767 column12, line 66 to column 13, line 19.

[0062] The amount of the photochromic compounds to be used in theimbibition composition, which is incorporated into a polymeric organichost material, is not critical provided that a sufficient amount is usedto produce a photochromic effect discernible to the naked eye uponactivation. Generally, such amount can be described as a photochromicamount. In the process of the present invention, this amount may betransferred onto the polymeric host all at once or by first transferringa portion of the amount in one step followed by the remainder in one ormore subsequent transfers prior to, after or with the transfer of aphotochromic performance improving amount of KEA. The particular amountused depends often upon the intensity of color desired upon irradiationthereof and upon the method used to incorporate the photochromiccomposition. Typically, the more photochromic compound incorporated, thegreater is the color intensity up to a certain limit.

[0063] The relative amounts of the aforesaid photochromic compounds usedwill vary and depend in part upon the relative intensities of the colorof the activated species of such compounds, the ultimate color desiredand the method of application of the photochromic composition to thepolymeric substrate. In a typical commercial imbibition process, theamount of total photochromic compound incorporated into a receptivepolymeric substrate may range from about 0.05 to about 2.0, e.g., from0.2 to about 1.0, milligrams per square centimeter of surface to whichthe photochromic compound is incorporated or applied.

[0064] The amount of photochromic compound incorporated into theimbibition composition may range from 0.1 to 99.9 weight percent basedon the weight of the composition. In one series of contemplatedembodiments in which the imbibition composition is a combination of KEAand photochromic compound, the amount of photochromic compound rangesfrom 25 to 99 weight percent, from 50 to 98 weight percent or from 70 to97 weight percent. The amount of photochromic compounds used in theimbibition composition of the present invention may range between anycombination of these values, inclusive of the recited ranges, e.g., from0.15 to 99.85 weight percent.

[0065] In another series of contemplated embodiments in which there arethree or more components in the imbibition composition, the amount ofphotochromic compound is equivalent to the amount of KEA, e.g., 5 weightpercent of each; is less than the amount of KEA, e.g., 4 weight percentphotochromic and 16 weight percent KEA; or is more than the amount ofKEA, e.g., 40 weight percent photochromic compound and 10 weight percentKEA. The sum of all the components in the imbibition composition is 100percent.

[0066] In a further series of contemplated embodiments, the photochromiccompounds are included in imbibition composition A while the KEA(s) areincluded in imbibition composition B. An organic polymeric host could betreated with imbibition composition A follow-by treatment withimbibition composition B or vice a versa. Such treatments could be doneat different times, e.g., a lens could be treated with imbibitioncomposition A, shipped to another processing facility and later treatedwith imbibition composition B.

[0067] In a still further series of contemplated embodiments, a portionof the photochromic performance improving amount of kinetic enhancingadditives is transferred prior to transferring the photochromiccompounds and the remainder of the photochromic performance improvingamount of kinetic enhancing additives. Alternatively, a portion of thephotochromic amount of photochromic compounds is transferred prior totransferring the kinetic enhancing additives and the remainder of thephotochromic amount of photochromic compounds. A process in which aportion of the photochromic performance improving amount of kineticenhancing additives and a portion of the photochromic amount ofphotochromic compounds is transferred prior to transferring theremainder of each is also contemplated. In each of the aforementionedtransfer processes, one or more transfer or imbibition steps may beused.

[0068] The optional carrier of the present invention may be a solvent,i.e., an aqueous solvent, organic solvent or mixture of such solvents, apolymeric resin or a mixture of solvents and polymeric resin providedthat the carrier resin is not an epoxy resin. Examples ofsolvent-carriers include water, benzene, toluene, methyl ethyl ketone,acetone, ethanol, tetrahydrofurfuryl alcohol, n-methylpyrrolidone,2-ethoxyethyl ether, 2-methoxyethyl ether, xylene, cyclohexane, 3-methylcyclohexanone, ethyl acetate, tetrahydrofuran, methanol, methylpropionate, ethylene glycol, acetonitrile, butanol, methylisobutylketone, methylchloroform, isopropanol and mixtures of such solvents.Examples of polymeric resins include hydroxy (C₁-C₃)alkyl celluloses,poly(vinyl pyrrolidone) (PVP); mixtures of from 5 to 50 parts of hydroxy(C₁-C₃)alkyl celluloses and from 95 to 50 parts of PVP, polyvinylchloride, polyvinyl acetate, polyvinylbutyral, copolymers of vinylchloride and vinyl acetate, copolymers of vinyl chloride and vinylidenechloride, polyvinyl propionate, cellulose acetate butyrate, and mixturesof such polymeric resins.

[0069] When the carrier is a solvent, the imbibition composition may bedeposited on the surface of the polymeric substrate using a single stepimbibition process or a multiple step process which may include highboiling liquids and the application of ultrasonic energy as described inU.S. Pat. No. 5,789,015 or aqueous liquids and the application ofmicrowave radiation as described in U.S. Patent Publication No.20020040511A1; the imbibition composition may be applied to a temporarysupport such as a sheet of paper which is placed directly on thepolymeric substrate as described in U.S. Pat. No. 4,286,957; theimbibition composition may utilize a non-polar solvent, which is used ina two-layer immersion bath as described in U.S. Pat. No. 5,975,696; orthe imbibition composition may be used in a different method known inthe art for transferring such compositions into polymeric substrates,e.g., by vacuum deposition and thermal treatment as described in U.S.5,914,193.

[0070] When the carrier in the imbibition composition includes apolymeric resin, the resin essentially serves as a film-forming binderfor the other components of the composition. The affinity between thecarrier and the other components, i.e., the solubility of thephotochromic compounds and the KEA in the carrier, should be sufficientto form a homogeneous solution and permit ready removal or transfer ofthese compounds from the resin film at the aforementionedconcentrations. Also, the polymeric resin should not adhere strongly tothe polymeric substrate to which it is applied so that it can be readilyremoved from the surface of the substrate without leaving marks on thesurface.

[0071] Adjuvant materials may also be incorporated into the imbibitioncomposition. For example, ultraviolet light absorbers and/or stabilizersmay be included to improve the fatigue resistance of the photochromicsubstances. Adjuvants, such as hindered amine light stabilizers (HALS),antioxidants, e.g., polyphenolic antioxidants, ultraviolet lightabsorbers, such as asymmetric diaryloxalamide (oxanilide) compounds, andsinglet oxygen quenchers, e.g., a nickel ion complete with an organicligand, or mixtures of such materials are contemplated. They may be usedalone, in combination or in combination with the additional conventionalingredients described hereinafter. Such stabilizers are described inU.S. Pat. Nos. 4,720,356, 5,391,327 and 5,770,115.

[0072] The imbibition compositions used in the process of the presentinvention may further comprise additional conventional ingredients thatimpart desired physical characteristics to the composition or theresultant layer; that are required for the process used to apply theimbibition composition to the substrate; and/or that enhance the layermade therefrom. Such additional ingredients include rheology controlagents, e.g., silica, and leveling agents, e.g., surfactants.

[0073] The imbibition composition, i.e., KEA, photochromic compounds,and optional ingredients, such as adjuvants and convention/ingredientscan be prepared by any conventional technique. For example, theindividual components may be mixed and used neat or may be dissolved inappropriate solvents before combining or each of the components may besequentially dissolved or incorporated into a suitable carrier, withheat, if necessary.

[0074] Alternatively, multiple-imbibition composition and imbibing stepsmay be used to produce the photochromic article of the presentinvention. In one contemplated embodiment, a first imbibitioncomposition is used for the photochromic compounds and stabilizers, asecond includes the KEA and a third imbibition composition includes boththe photochromic compound(s) and KEA(s).

[0075] The imbibition composition is applied to at least one principalsurface, i.e., a flat or curved surface other than the side of thepolymeric host, by techniques known in the art that are suitable toproduce a mottle-free coating or film of uniform thickness. In onecontemplated embodiment, the composition is applied in such a mannerthat the resulting film is substantially dry as soon as it is formed,i.e., the readily vaporizable solvent is substantially volatilized asthe composition is applied to the receptor surface of the plastic host,thereby leaving a substantially dry film. Application techniques thatmay be employed include spraying, brushing, curtain coating,spin-coating, dip coating and use of a draw-down blade or wire bar.

[0076] Before applying the imbibition composition to the polymeric host,the surface of the polymer to which the composition is to be applied ispreferably cleaned. Cleaning may be accomplished by washing the surfacewith an aqueous medium, e.g., soapy water, to remove dust and dirt;washing the surface with an organic solvent such as methylethylketone toremove any organic film present on the surface; and/or eliminatingstatic charges that are present on the surface of the plastic material.Elimination of static electricity can be accomplished by commerciallyavailable equipment which ionize the air above the surface, therebyproducing a conductive path which allows the static charge to drain offor otherwise be neutralized.

[0077] The surface of the plastic material to which the imbibitioncomposition is applied should be receptive to imbibition of thephotochromic compound(s) and KEA during the heating step. If thereceptor surface is not amenable to imbibition, it can be treated topermit improved diffusion of the photochromic composition into thesubsurface of the polymeric host, e.g., by physically or chemicallyetching the surface. A receptive surface can be achieved usually byundercuring slightly the polymer during its formation. Such techniquesare conventional in the polymerization art.

[0078] Following application of the imbibition composition to thesurface(s) of the polymeric organic host material, the substantially dryfilm or coating is permitted to completely dry. Drying can beconveniently conducted at room temperature in air; but, other conditionsof drying which avoid crystallization of the KEA, photochromic compoundor other ingredient within the resin film or coating may be used as theoccasion warrants. Thereafter, the coated polymeric article is heatedsubstantially uniformly at temperatures below the boiling temperature ofthe photochromic compound used. Heating can be accomplished by anyconvenient technique that results in substantially uniform heating ofthe coated polymeric host. In one contemplated embodiment, heating isaccomplished in a conventional hot air recirculating oven, which allowsfor uniform heating and hence a constant driving force for transfer ofthe photochromic compound and KEA into the polymeric host. Heating mayalso be accomplished in a vacuum or with use of an inert, e.g., nitrogenatmosphere.

[0079] The temperatures to which the coated polymeric article is heatedwill vary and depend on the boiling point and vapor pressure of theparticular photochromic compound and KEA utilized as well as thesoftening temperature of the synthetic polymeric article. Suchtemperatures should preferably be near to but below the boiling point ofthe photochromic compound and KEA and below the softening temperature ofthe synthetic polymeric article. Moreover, such temperatures, i.e.,photochromic transfer or incorporation temperatures, should be such asto avoid decomposition (pyrolysis) of the photochromic compound, as wellas the KEA. Hence, the transfer temperatures chosen are sufficient toraise the vapor pressure of the photochromic compound and KEA adequatelyto permit its transfer into the polymeric host without significantdecomposition to the compounds and softening of the polymeric host.

[0080] As the boiling points and vapor pressures of KEA and photochromiccompounds, e.g., chromene-type photochromic compounds, will varydepending on the nature of the compound and their substituents, onetemperature range applicable to all photochromic compositions cannot bedescribed. However, given the above requirements one skilled in the artcan readily determine an appropriate temperature for heating the coatedpolymeric article. Transfer temperatures of between 5° C. and 50° C.,less than the boiling temperature of the photochromic compound and theKEA are contemplated except where significant decomposition of thecompounds is experienced at such temperatures. Generally, in theimbibition art, temperatures used in association with organicphotochromic compounds and polymeric lenses are between 100° C. and 160°C. In one contemplated embodiment, a transfer temperature of between 5and 10° C. less than the boiling temperature of the photochromiccompound and other transferable components is used.

[0081] The coated polymeric article is maintained at the above-describedtransfer temperatures, for a time sufficient to allow a substantialportion, i.e., a photochromic amount, of the photochromic compound and aphotochromic performance improving amount of KEA, to diffuse into andpenetrate beneath the surface of the plastic article. Typically, theheating period in commercial imbibition processes is from one hour totwelve hours, usually between four and nine hours at the transfertemperatures. When multiple imbibition compositions and imbibition stepsare employed to separately transfer the photochromic compound(s),kinetic enhancing additives and/or combinations thereof, different timeintervals for each step may be required to cost effectively produce aphotochromic article demonstrating improved performance.

[0082] The mechanism by which the photochromic compound and the KEAtransfer from the imbibition composition, resin film or coating adheredto the surface of the polymeric host into the polymeric host materialhas not been established with certainty. It is postulated that thermaldiffusion, sublimation and condensation or a combination of theaforesaid mechanisms may accomplish transfer. Whatever the specificmechanism(s), the photochromic compound and the KEA permeate into thepolymeric substrate, usually into the subsurface regions thereof, andbecome incorporated within the polymeric host material. In this manner,a photochromic amount of the photochromic substance and a photochromicperformance improving amount of KEA are transferred into and across theplanar surface of the plastic host.

[0083] Following transfer of the photochromic and kinetic enhancingadditive into the polymeric article, the coated polymer is allowed tocool, e.g., to room temperature, and subsequently the residual coatingor resin film, its concentration of the KEA and photochromic compoundsreduced, is removed from the surface of the polymeric host. Removal ofthe photochromic compound and KEA-depleted film may be accomplished byany suitable technique; preferably a technique that does not impair theoptical quality of the surface of the plastic. Conveniently, thedepleted film is stripped from the polymeric substrate by contacting thefilm with a suitable solvent such as soapy water or organic solventssuch as trichloroethylene, methylethylketone, methylisobutylketone,methylethylketone-toluene mixture, or other solvents such as: acetone,ethylene dichloride, chloroform and chlorobenzenes. The same solventused to prepare the imbibition composition may be used to remove theresidual resin film.

[0084] A suitable method for contacting the film or coating with organicsolvent is in a vapor degreasing unit wherein the coated substrate isexposed to the vapors of the selected solvent(s) which condense on andrun off the surface of the polymeric material, thereby washing thephotochromic and/or KEA-depleted resin film or coating from the surface.Alternatively, the resin film or coating can be removed by dipping thepolymeric substrate into a bath of the solvent, spraying the solvent onthe coated substrate or physically stripping the film or coating fromthe substrate. After the photochromic and KEA-depleted or spent film orcoating has been removed from the surface of the polymeric article, thesurface can be washed with water, solvent or a suitable aqueous mediumsuch as, for example, soap or detergent solutions and dried. If desired,the polymeric article can be tinted with conventional disperse andsoluble dyes used in the tinting of organic plastic materials usingtechniques well known in the art, e.g., a conventional dye bath.Thereafter, the tinted polymeric article is washed, e.g., with soapywater, and dried. Tinting of the polymeric article can be performedimmediately after removal of the spent resin film or coating and beforecleaning the surface. Alternatively, tinting can be performed before thephotochromic composition is applied.

[0085] The polymeric host material will usually be transparent, but maybe translucent or even opaque. The host material need only be perviousto that portion of the electromagnetic spectrum, which activates thephotochromic substance, i.e., that wavelength of ultraviolet (UV) lightthat produces the open or colored form of the substance and that portionof the visible spectrum that includes the absorption maximum wavelengthof the substance in its UV activated form, i.e., the open form.

[0086] In one contemplated embodiment, the color of the host is suchthat it does not mask the color of the activated form of thephotochromic compounds, i.e., so the change in color is readily apparentto the observer. In another contemplated embodiment, the polymericorganic host material is a solid transparent or optically clearmaterial, e.g., materials suitable for optical applications, such asplano, ophthalmic and contact lenses, windows, automotivetransparencies, e.g., windshields, aircraft transparencies, plasticsheeting, polymeric films, etc.

[0087] One polymeric organic host material which may be used with thephotochromic imbibition composition described herein is anon-elastomeric poly(urea-urethane). Non-elastomeric poly(urea-urethane)is defined herein as the reaction product of reactants comprising (a) atleast one polyol, e.g., diol; (b) at least one polyisocyanate having atleast two isocyanato groups; (c) at least one polyamine having at leasttwo amino groups, each amino group being independently selected fromprimary amino and secondary amino; and optionally, (d) at least onepolyol having at least three hydroxyl groups. In one contemplatedembodiment, the number of isocyanato groups of the isocyanate reactantsis greater than the number of hydroxyl groups of the polyol reactants.

[0088] The preparation of poly(urea-urethane) is described in U.S.patent application Ser. No. 09/766,554, filed Jan. 19, 2001 and in U.S.Pat. Nos. 3,866,242; 5,811,506; 5,962,617; and 5,962,619.

[0089] Examples of additional polymeric organic host materials which maybe used with the imbibition composition described herein include:polymers, i.e., homopolymers and copolymers, of polyol(allyl carbonate)monomers, e.g., diethylene glycol bis(allyl carbonate) monomers,polyfunctional acrylate monomers, polyfunctional methacrylate monomers,diethylene glycol dimethacrylate monomers, diisopropenyl benzenemonomers, ethoxylated bisphenol A dimethacrylate monomers, ethyleneglycol bismethacrylate monomers, poly(ethylene glycol) bismethacrylatemonomers, ethoxylated phenol bismethacrylate monomers, alkoxylatedpolyhydric alcohol acrylate monomers, such as ethoxylated trimethylolpropane triacrylate monomers, diallylidene pentaerythritol monomers,urethane acrylate monomers, such as those described in U.S. Pat. No.5,373,033, and vinylbenzene monomers, such as those described in U.S.Pat. No. 5,475,074 and styrene; polymers, i.e., homopolymers andcopolymers, mono- or polyfunctional, e.g., di- or multi-functional,acrylate and/or methacrylate monomers, poly(C₁-C₁₂ alkyl methacrylates),such as poly(methyl methacrylate), poly(oxyalkylene)dimethacrylate,poly(alkoxylated phenol methacrylates), cellulose acetate, cellulosetriacetate, cellulose acetate propionate, cellulose acetate butyrate,poly(vinyl acetate), poly(vinyl alcohol), poly(vinyl chloride),poly(vinylidene chloride), polyurethanes, polythiourethanes,thermoplastic polycarbonates, polyesters, poly(ethylene terephthalate),polystyrene, poly(alpha methylstyrene), copoly(styrene-methylmethacrylate), copoly(styrene-acrylonitrile), polyvinylbutyral andpolymers, i.e., homopolymers and copolymers, of diallylidenepentaerythritol, particularly copolymers with polyol (allyl carbonate)monomers, e.g., diethylene glycol bis(allyl carbonate), and acrylatemonomers, e.g., ethyl acrylate, butyl acrylate. Further examples ofpolymeric organic host materials are disclosed in the U.S. Pat. No.5,753,146, column 8, line 62 to column 10, line 34.

[0090] Transparent copolymers and blends of transparent polymers arealso suitable as host materials. In one contemplated embodiment, thehost material or substrate for the imbibition composition is anoptically clear polymerized organic material prepared from athermoplastic polycarbonate resin, such as the carbonate-linked resinderived from bisphenol A and phosgene, which is sold under thetrademark, LEXAN; a polyester, such as the material sold under thetrademark, MYLAR; a poly(methyl methacrylate), such as the material soldunder the trademark, PLEXIGLAS; polymerizates of a polyol(allylcarbonate) monomer, especially diethylene glycol bis(allyl carbonate),which monomer is sold under the trademark CR-39, and polymerizates ofcopolymers of a polyol (allyl carbonate), e.g., diethylene glycolbis(allyl carbonate), with other copolymerizable monomeric materials,such as copolymers with vinyl acetate, e.g., copolymers of from 80-90percent diethylene glycol bis(allyl carbonate) and 10-20 percent vinylacetate, particularly 80-85 percent of the bis(allyl carbonate) and15-20 percent vinyl acetate, and copolymers with a polyurethane havingterminal diacrylate functionality, as described in U.S. Pat. Nos.4,360,653 and 4,994,208; and copolymers with aliphatic urethanes, theterminal portion of which contain allyl or acrylyl functional groups, asdescribed in U.S. Pat. No. 5,200,483; poly(vinyl acetate),polyvinylbutyral, polyurethane, polymers of diethylene glycoldimethacrylate monomers, diisopropenyl benzene monomers, ethoxylatedbisphenol A dimethacrylate monomers, ethylene glycol bismethacrylatemonomers, poly(ethylene glycol) bismethacrylate monomers, ethoxylatedphenol bismethacrylate monomers and ethoxylated trimethylol propanetriacrylate monomers; cellulose acetate, cellulose propionate, cellulosebutyrate, cellulose acetate butyrate, polystyrene and copolymers ofstyrene with methyl methacrylate, vinyl acetate and acrylonitrile.

[0091] More particularly contemplated is use of the imbibitioncomposition of the present invention with optical organic resin monomersused to produce optically clear polymeric coatings and polymerizates,i.e., materials suitable for optical applications, such as lenses foruse in a pair of spectacles, e.g., plano or ophthalmic spectacle lenses,or for use as contact lenses. Optically clear polymerizates may have arefractive index that may range from about 1.35 to about 1.75, e.g.,from about 1.495 to about 1.66.

[0092] Other examples of polymeric organic host materials arethermoplastic or thermosetting coatings described in the Kirk-OthmerEncyclopedia of Chemical Technology, Fourth Edition, Volume 6, pages 669to 760. In one contemplated embodiment, thermosetting coatings are used.The photochromic or nonphotochromic polymeric coating applied to thesurface of the substrate and imbibed with the imbibition composition ofthe present invention containing KEA and/or photochromic compounds maybe a coating that upon curing forms a polymeric layer selected frompolyurethanes, aminoplast resins, polysilanes, poly(meth)acrylates,e.g., polyacrylates and polymethacrylates, polyanhydrides,polyacrylamides, or epoxy resins, e.g., polyacid cured epoxy resins.

[0093] Specifically contemplated as host materials are polymerizates ofSpectralite® lenses sold by Sola International, TRIVEX™ lenses andoptical resins sold by PPG Industries, Inc. under the CR- designation,e.g., CR-307 and CR-407, and polymerizates prepared for use as hard orsoft contact lenses. Methods for producing both types of contact lensesare disclosed in U.S. Pat. No. 5,166,345, column 11, line 52, to column12, line 52. Additional polymerizates contemplated for use with thephotochromic compositions of the present invention are polymerizatesused to form soft contact lenses with high moisture content described inU.S. Pat. No. 5,965,630 and extended wear contact lenses described inU.S. Pat. No. 5,965,631.

[0094] Photochromic articles prepared using the imbibition compositionof the present invention may be coated with a silica, titania, and/orzirconia-based hard coating material. Alternatively, an organic hardcoating material of the ultraviolet curable type may be applied so as toform a hard surface layer. Application of such protective coatings,e.g., abrasion resistant coatings, may be by any of the methods used incoating technology such as, for example, spray coating, spin coating,spread coating, curtain coating, dip coating or roll-coating. Othercoatings and/or surface treatments, e.g., antireflective surface,hydrophobic coating, etc., may also be applied individually orsequentially to at least one surface of the photochromic articles of thepresent invention. An antireflective coating, e.g., a monolayer ormultilayer of metal oxides, metal fluorides, or other materials, may bedeposited onto the photochromic articles, e.g., lenses, of the presentinvention through vacuum evaporation, sputtering, or some other method.

[0095] The present invention is more particularly described in thefollowing examples that are intended as illustrative only, sincenumerous modifications and variations therein will be apparent to thoseskilled in the art.

[0096] Examples 1-3 and Comparative Example 1 demonstrate the effects onthe Photochromic Performance Rating of including 5 grams oftrimethylolpropane triglycidyl ether (TMPTGE), poly(ethylene glycol)diglycidyl ether (PEG(DGE)) or polycaprolactone diol (PCLD) in the firstphotochromic imbibition composition as compared to the firstphotochromic imbibition composition without kinetic enhancing additive(KEA).

[0097] Examples 4-10 and Comparative Example 2 demonstrate the effectson the Photochromic Performance Ratings of including 5 grams of TMPTGE,PEG(DGE), PCLD, Poly(ethylene glycol)600 (PEG-600), polytetrahydrofuran(PTHF), poly(ethylene glycol)900 (PEG-900) and 1,6-hexane diol (HD) inthe second photochromic imbibition composition as compared to the secondphotochromic imbibition composition without KEA. The results of testingon Examples 1-10 and CE 1 and 2 are included in Table 1.

[0098] Examples 11, 12 and CE1 were used in two step imbibition studiesto demonstrate the effects on the Photochromic Performance Rating ofimbibing Example 11 containing 15% TMPTGE without photochromic compoundsfollowed by CE1 or Example 12 containing 10% TMPTGE in the firstphotochromic imbibition composition as compared to only imbibing CE1 orExample 12. The results are listed in Table 2.

[0099] Examples 12, 15, CE1 and CE2 were used in two step imbibitionstudies to demonstrate the effects on the Photochromic PerformanceRating of first imbibing CE1 or CE2 followed by the imbibition ofExample 12 or Example 15 containing 10% TMPTGE in the secondphotochromic imbibition composition over a period of 1,2 and 3 hours ascompared to imbibing only CE1 or CE2. The results are listed in Table 3.

[0100] Examples 12, 13 (10% PEG-900) 14 (10% PCLD) and CE1 were used ina study in which the imbibed lenses were coated with HI-GARD® 1030 asolgel-type hardcoating solution (HC); HI-GARD® 1030 solution andReflection Free antireflective coating (HC & AR); or no coating wasapplied. The effects of the coatings on the Photochromic PerformanceRating as well as the adhesion of the coatings to the lenses was tested.These results are listed in Table 4.

[0101] Example 15 (10% TMPTGE), 16 (10% PEG-900), 17 (10% PCLD) and CE2were tested in the same way as Examples 12, 13, 14 and CE1. The resultsare listed in Table 5.

[0102] Examples 15, 17, 18 (5% TMPTGE and 5% PCLD) and CE2 demonstratethe effects of mixing two KEA's on the Photochromic Performance Ratingas compared to testing single KEA's or no KEA. These results are listedin Table 6.

[0103] Example 19 and CE3 demonstrate the effects on the PhotochromicPerformance Rating of using the first poly(urea-urethane) substrateimbibed with PEG(DGE) in the third photochromic imbibition compositionas compared to the CE3 without PEG(DGE). Results are listed in Table 7.

[0104] Example 20 and CE4 demonstrate the effects on the PhotochromicPerformance Rating of using the second poly(urea-urethane) substrateimbibed with PEG(DGE) in the third photochromic imbibition compositionas compared to CE4 without PEG(DGE). Results are listed in Table 7.

[0105] Examples 21, 22 and CE5 demonstrate the effect on thePhotochromic Performance Rating of using the first poly(urea-urethane)substrate imbibed with PCLD or PEG-900 in the fourth photochromicimbibition composition as compared to CE5 without PCLD or PEG-900.Results are listed in Table 7.

[0106] Examples 23, 24 and CE6 demonstrate the effect on thePhotochromic Performance Rating of using the second poly(urea-urethane)substrate imbibed with PCLD or PEG-900 in the fourth photochromicimbibition composition as compared to CE6 without PCLD or PEG-900.Results are listed in Table 7.

EXAMPLE 1

[0107] The following materials were added in the order and the mannerdescribed to a container suitable for use with a BRINKMAN PT-3000homogenizer: Material Weight (grams) Charge-1 2-Ethoxy ethyl ether 50.0Tetrahydrofurfuryl alcohol 30.0 n-Methyl pyrrolidone 20.0 (TMPTGE)⁽¹⁾5.0 Hydroxypropyl cellulose 12.0 Silica 0.9 Charge-2 Photochromic No.1⁽²⁾ 2.28 Photochromic No. 2⁽³⁾ 0.48 Photochromic No. 3⁽⁴⁾ 0.54Photochromic No. 4⁽⁵⁾ 2.70 TINUVIN ® 144 UV Stabilizer⁽⁶⁾ 2.10 IRGANOX ®3114 Antioxidant⁽⁷⁾ 0.90

EXAMPLE 2

[0108] The procedure of Example 1 was followed except thattrimethylolpropane triglycidyl ether was replaced by an equal amount ofpoly(ethylene glycol)diglycidyl ether (PEG(DGE)) having a number-averagemolecular weight of 526.

EXAMPLE 3

[0109] The procedure of Example 1 was followed except thattrimethylolpropane triglycidyl ether was replaced by an equal amount ofpolycaprolactone diol (PCLD) having an number-average molecular weightof 530.

COMPARATIVE EXAMPLE 1

[0110] The procedure of Example 1 was followed except thattrimethylolpropane triglycidyl ether was not included in the imbibitionformulation.

EXAMPLE 4

[0111] The procedure of Example 1 was followed except that the followingmaterials were used in Charge 2. Material Weight (grams) PhotochromicNo. 5⁽⁸⁾ 2.16 Photochromic No. 6⁽⁹⁾ 0.54 Photochromic No. 7⁽¹⁰⁾ 3.00Photochromic No. 3 0.30 Tinuvin ® 144 UV Stabilizer 0.60 Irganox ® 3114Antioxidant 1.2 Sanduvor 3058 UV Stabilizer⁽¹¹⁾ 1.2

EXAMPLE 5

[0112] The procedure of Example 4 was followed except thattrimethylolpropane triglycidyl ether was replaced with an equal amountof poly(ethylene glycol)diglycidyl ether (PEG(DGE)) having anumber-average molecular weight of 526.

EXAMPLE 6

[0113] The procedure of Example 4 was followed except thattrimethylolpropane triglycidyl ether was replaced with an equal amountof polycaprolactone diol (PCLD) having a number-average molecular weightof 530.

EXAMPLE 7

[0114] The procedure of Example 4 was followed except that trimethylolpropane triglycidyl ether was replaced with an equal amount ofpoly(ethylene glycol) (PEG-600) having an number-average molecularweight of 600.

EXAMPLE 8

[0115] The procedure of Example 4 was followed except that trimethylolpropane triglycidyl ether was replaced with an equal amount ofTERETHANE® 650 polyether glycol (PTHF) reported to bepolytetrahydrofuran linear-chain polymer having a number-averagemolecular weight of 650.

EXAMPLE 9

[0116] The procedure of Example 4 was followed except that trimethylolpropane triglycidyl ether was replaced with an equal amount ofpoly(ethylene glycol) (PEG-900) having an number-average molecularweight of 900.

EXAMPLE 10

[0117] The procedure of Example 4 was followed except that trimethylolpropane triglycidyl ether was replaced with an equal amount of1,6-hexanediol (HD).

COMPARATIVE EXAMPLE 2

[0118] The procedure of Example 4 was followed except thattrimethylolpropane triglycidyl ether was not included in the imbibitionformulation.

EXAMPLE 11

[0119] The procedure of Example 1 was followed except thattrimethylolpropane triglycidyl ether was used at a level of 15 percentby weight, based on the total weight of Charge-1. Charge-2 was not used.

EXAMPLE 12

[0120] The procedure of Example 1 was followed except thattrimethylolpropane triglycidyl ether was used at a level of 10 percentby weight, based on the total weight of Charges 1 and 2.

EXAMPLE 13

[0121] The procedure of Example 12 was followed except thattrimethylolpropane triglycidyl ether was replaced by poly(ethyleneglycol) (PEG-900).

EXAMPLE 14

[0122] The procedure of Example 12 was followed except thattrimethylolpropane triglycidyl ether was replaced by polylcaprolactonediol (PCLD).

EXAMPLE 15

[0123] The procedure of Example 4 was followed except thattrimethylolpropane triglycidyl ether was used at a level of 10 percentby weight, based on the total weight of Charge 1 and 2.

EXAMPLE 16

[0124] The procedure of Example 15 was followed except thattrimethylolpropane triglycidyl ether was replaced by poly(ethyleneglycol) (PEG-900).

EXAMPLE 17

[0125] The procedure of Example 15 was followed except thattrimethylolpropane triglycidyl ether was replaced by polycaprolactonediol (PCLD).

EXAMPLE 18

[0126] The procedure of Example 15 was followed except thattrimethylolpropane triglycidyl ether was used at a level of 5 percent byweight and 5 percent by weight of polycaprolactone diol was added.

EXAMPLE 19 Part A

[0127] The following materials were added in the order and the mannerdescribed to a suitable reaction vessel equipped with an agitator, athermometer, nitrogen inlet and heat/cooling capabilities. Number ofMaterial Equivalents PCLD (400 EW)⁽¹²⁾ 0.740 PCLD (200 EW)⁽¹³⁾ 0.115PCLD (1000 EW)⁽¹⁴⁾ 0.025 Trimethylolpropane 0.120 DESMODUR W⁽¹⁵⁾ 2.700

[0128] After addition of the materials, nitrogen was introduced into thevessel to provide a nitrogen blanket and the agitator was turned on.Heat was applied until the prepolymer reaction mixture reached atemperature of 250° F. (121° C.). Further heating was discontinued. Theresulting exothermic reaction usually caused an increase in thetemperature of the reaction mixture to about 280° F. (138° C.). If thetemperature continued to rise above 280° F. (138° C.), cooling wasapplied. After the reaction temperature reached about 220° F. (104° C.),the prepolymer product was filtered through a 400 mesh filter. Theresulting filtrate was cooled and transferred to a suitable container.

Part B

[0129] The following materials were added in the order and the mannerdescribed to a reaction injection molding (RIM) machine, such as the MaxMixer available from Max Machines: Material Weight (grams) Charge-1Product of Part A 50.00 Charge-2 Diethyltoluenediamine 12.50

[0130] Charge-1 was added to the container. Charge-2 was added and thecontents were rapidly mixed in the Max Mixer.

Part C

[0131] The product of Part B was poured into molds measuring 60-80 mmthat were treated with an external mold release agent, preheated to 150°C. and placed in an oven at 150° C. for 16 hours. Afterwards, thepolymerizates were removed from the molds.

Part D

[0132] The following materials were added in the order and the mannerdescribed to a container suitable for use with a BRINKMAN PT-3000homogenizer: Material Weight (grams) Charge-1 2-Ethoxy ethyl ether 30.0Tetrahydrofurfuryl alcohol 35.0 n-Methyl pyrrolidone 20.0 PEG(DGE) 10.0Hydroxypropyl cellulose 12.0 Silica 0.9 Charge-2 Photochromic No. 1 4.3Photochromic No. 2 1.7 SANDUVOR 3056 UV stabilizer 1.8 IRGANOX ® 3114antioxidant 1.2

[0133] Charge-1 was added to the container and mixed by the homogenizerat a speed of 5000 rpm for 2 minutes or until the materials weredissolved. Charge-2 was added and the resulting mixture was heated andmixed until the materials were dissolved.

Part E

[0134] The solutions of Part D were imbibed into duplicate sample lensesprepared in Part C by applying the imbibition formulation onto thesurface of the test lenses by spin coating. The average wet weight ofthe resin film that formed on the lens ranged from 0.35 to 0.40milligrams per lens. The resin film was allowed to dry. The lenses werethen heated in a hot-air oven at 135-140° C. for 8 hours. After cooling,the resin film was removed from the test samples by rinsing with waterand wiping with an acetone soaked tissue.

COMPARATIVE EXAMPLE 3

[0135] The procedure of Example 19 was followed except that polyethyleneglycol diglycidyl ether was not included in Charge-1 of Part D. Theamount of hydroxypropyl cellulose and silica remained the same. Theamounts of the other materials were as follows: Material Weight (grams)2-Ethoxy ethyl ether 35 Tetrahydrofurfuryl alcohol 35 n-Methylpyrrolidone 20

EXAMPLE 20

[0136] The procedure of Example 19 was followed except that thefollowing formulation was used in Part A to prepare the prepolymer.Number of Material Equivalents PCLD (400 EW) 0.75 PCLD (200 EW) 0.10Trimethylolpropane 0.15 DESMODUR W 2.70

COMPARATIVE EXAMPLE 4

[0137] The procedure of Example 20 was followed except that polyethyleneglycol diglycidyl ether was not included in Charge-1 of Part D. Theamount of hydroxypropyl cellulose and silica remained the same. Theamounts of the other materials were the same as in Comparative Example3.

EXAMPLE 21

[0138] The procedure of Example 19 was followed except that in Charge-1of Part D, polyethylene glycol diglycidyl ether (10 grams) was replacedwith polycaprolactone diol (PCLD) (6.67 grams) having an number-averagemolecular weight of 530 and the following materials were used inCharge-2. Material Weight (grams) Photochromic No. 3 2.28 PhotochromicNo. 4 0.48 Photochromic No. 5 0.54 Photochromic No. 6 2.70 TINUVIN ® 144UV Stabilizer 2.1 IRGANOX ® 3114 antioxidant 0.9

EXAMPLE 22

[0139] The procedure of Example 21 was followed except that in Charge-1of Part D, polycaprolactone diol was replaced with an equal amount ofpolyethylene glycol (PEG-900) having an number-average molecular weightof 900.

COMPARATIVE EXAMPLE 5

[0140] The procedure of Example 21 was followed except thatpolycaprolactone diol was not included in Charge-1 of Part D. The amountof hydroxypropyl cellulose and silica remained the same. The amounts ofthe other materials were the same as in Comparative Example 3.

EXAMPLE 23

[0141] The procedure of Example 22 was followed except that thefollowing formulation was used in Part A to prepare the prepolymer.Number of Material Equivalents PCLD (400 EW) 0.75 PCLD (200 EW) 0.10Trimethylolpropane 0.15 DESMODUR W 2.70

EXAMPLE 24

[0142] The procedure of Example 22 was followed except that thefollowing formulation was used in Part A to prepare the prepolymer.Number of Material Equivalents PCLD (400 EW) 0.75 PCLD (200 EW) 0.10Trimethylolpropane 0.15 DESMODUR W 2.70

COMPARATIVE EXAMPLE 6

[0143] The procedure of Example 23 was followed except thatpolycaprolactone diol was not included in Charge-1 of Part D. The amountof hydroxylpropyl cellulose and silica remained the same. The amounts ofthe other materials were the same as in Comparative Example 3.

EXAMPLE 25 Part A

[0144] Testing of Examples 1-18 and Comparative Examples (CE) 1 and 2was done with sample lenses cast from an optical resin sold by PPGIndustries, Inc. under the designation CR-307. The sample lenses werewashed with dishwashing detergent and water, rinsed with deionized waterand wiped with an acetone soaked tissue prior to the application of theexample solutions. The solutions of the Examples and ComparativeExamples were imbibed into the sample lenses by applying a film of theimbibition formulation onto the surface of the test lenses by spincoating. The average wet weight of the resin film ranged from 0.35 to0.40 milligrams per lens. The applied film was allowed to dry. Thelenses were then heated in a hot-air oven at 135-140° C. fo r the timeindicated in the tables. After cooling, the resin film was removed fromthe test samples by rinsing with water and wiping with an acetone soakedtissue. When a second imbibition step was included, as reported inTables 2 and 3, it was done after removal of the first imbibition resinfilm.

Part B

[0145] The photochromic lenses prepared in Part A and the lenses ofExamples 19-24 and Comparative Examples 3-6 were screened forultraviolet absorbance and lenses having comparable UV absorbance at 390nanometers were tested for photochromic response on an optical bench.Most lenses were tested in duplicate and the results were averagedexcept the lenses subjected to adhesion testing reported in Tables 4 and5, for which single lenses were tested and the lenses whose results arereported in Tables 6 and 7. The ultraviolet absorbance value gives anindication of the amount of photochromic compounds in the lens. Theoptical bench was maintained at a temperature of 72° F. (22° C.). Thelenses of Examples 19-24, and Comparative Examples 3-6 were activatedfor 15 minutes and the ΔOD was measured after the first 30 seconds andthen after 15 minutes. The other imbibed lenses were activated for 15minutes and the ΔOD was measured after 15 minutes.

[0146] Prior to testing on the optical bench, the photochromic testsquares were exposed to 365 nm ultraviolet light for about 10 minutes ata distance of about 14 cm from the lamps to activate the photochromiccompound. The samples were then placed under a halogen lamp (500W, 120V)for about 10 minutes at a distance of about 36 cm from the lamp tobleach, or inactivate, the photochromic compound in the samples. Thetest squares were then kept in a dark environment for at least 1 hourprior to testing on the optical bench. The bench comprises a rail towhich was fitted a 300 watt Xenon arc lamp, a remote controlled shutter,a Schott 3 mm KG-2 band-pass filter, which removed short wavelengthradiation, neutral density filter(s), a quartz water cell/sample holderfor maintaining sample temperature in which the test sample to be testedwas inserted.

[0147] Measurements were made on the optical bench with the power outputadjusted to 6.7 Watts per square meter. Measurement of the power outputwas made using an International Light Research Radiometer (Model #:IL1700; Serial #: 1290) with a radiometer detector (Model #: SED 033;Serial #: 5886) or comparable equipment. The radiometer was placed in anoptical rail carrier on the rail at the correct focal length and thelight output was measured. Adjustments to the power output were made byincreasing or decreasing the lamp wattage or by adding or removingneutral density filters in the light path.

[0148] The test samples were exposed to UV irradiation using a Xenon arclamp at 300 normal to the surface of the test sample. A monitoring,collimated beam of light from the tungsten/halogen lamp maintainedperpendicular to the test sample was passed through it and then directlyinto an integrating sphere attached to a spectrophotometer. Theintegrating sphere is a device to collect and mix all of monitoringlight that passes through the test sample. The control of the testconditions and acquisition of the data was handled by a proprietaryprogram in conjunction with OOIBased 32 software provided by OceanOptics, Inc.

[0149] Change in optical density (ΔOD) from the bleached state to thedarkened state was determined by establishing the initial transmittance,opening the shutter from the Xenon lamp to provide ultraviolet radiationto change the test lens from the bleached state to an activated (i.e.,darkened) state at selected intervals of time, measuring thetransmittance in the activated state, and calculating the change inoptical density according to the formula: ΔOD=log(% Tb/% Ta), where % Tbis the percent transmittance in the bleached state, % Ta is the percenttransmittance in the activated state and the logarithm is to the base10.

[0150] The Bleach Rate (T ½) is the time interval in seconds for the ΔODof the activated form of the photochromic compound in the lenses toreach one half the highest ΔOD after removal of the source of activatinglight, i.e., shutter closed.

[0151] Results for the photochromic imbibed lenses of: Examples 1-10 andComparative Examples 1 and 2 are listed in Table 1; of Examples 11 and12 and Comparative Examples 1 and 2 using dual imbibition steps arelisted in Tables 2 and 3; Examples 12-17 and Comparative Examples 1 and2 to which a commercial hardcoat or a hardcoat and antireflectioncoatings were applied and also tested for adhesion on single lensesafter being held in boiling water for 1 hour using ASTM D-3359 StandardTest Method for Measuring Adhesion by Tape Test-Method B are listed inTables 4 and 5; Examples 15, 17 and 18, which includes a mixtures of anepoxy-containing compound and an organic polyol in Example 18, in Table6; and Example 19 to 24 and Comparative Examples 3-6, which utilizepoly(urea-urethane) lenses, in Table 7. An abbreviation identifying thekinetic enhancing additive (KEA) used in the examples is included withthe Example No. in each Table.

[0152] The results of Examples 1-3 and 11-14 should be compared toComparative Example 1, Examples 4-10 and 15-18 should be compared toComparative Example 2, Example 19 should be compared to ComparativeExample 3, Example 20 should be compared to Comparative Example 4,Examples 21 and 22 should be compared to Comparative Example 5, andExamples 23 and 24 should be compared to Comparative Example 6.

[0153] It is important that the substrate of the Comparative Example isfrom the same batch of material used to produce the substrate of theExamples. This is done to avoid the effects of any variation in thebatches on the outcome of the Photochromic Performance Test.

[0154] Also included in the Tables is a Performance Rating resultingfrom the Photochromic Performance Test. The Photochromic PerformanceTest utilizes the ΔOD at 15 minutes and Bleach Rate results to determinea rating of the photochromic performance. The Performance Rating iscalculated by dividing the A OD at 15 minutes by the T 1/2 andmultiplying the result by 10,000. The higher the Performance Rating, themore kinetically enhanced the photochromic compounds are as compared tothe Comparative Examples without the additive of the present invention.TABLE 1 Example No. Imbibition ΔOD@15 T ½ Performance (KEA) Time (hrs.)minutes seconds Rating 1 (TMPTGE) 7 0.64 112 57.1 2 (PEG(DGE)) 7 0.42102 41.2 8 0.56 120 46.7 3 (PCLD) 8 0.57 121 47.1 CE 1 8 0.59 177 33.3 4(TMPTGE) 7 0.48 73 65.8 5 (PEG(DGE)) 7 0.37 67 55.2 8 0.45 81 55.6 6(PCLD) 8 0.43 87 49.4 7 (PEG-600) 8 0.45 95 47.4 8 (PTHF) 8 0.45 90 50.09 (PEG-900) 8 0.44 81 54.3 10 (HD) 8 0.55 132 41.7 CE 2 8 0.55 141 39.0

[0155] TABLE 2 Time for Time for First Imbibition Imbibition @ SecondImbibition Imbibition @ ΔOD@15 T ½ Example No. 135° C. Example No. 135°C. minutes seconds Performance Rating 11 (TMPTGE) 3 hours CE 1 7 hours0.59 158 37.3 11 (TMPTGE) 3 hours 12 (TMPTGE) 7 hours 0.57 126 45.2 — —CE 1 7 hours 0.58 196 29.6 — — 12 (TMPTGE) 7 hours 0.60 147 40.8

[0156] TABLE 3 Time for Time for First Imbibition Imbibition @ SecondImbibition Imbibition @ ΔOD@15 T ½ Example No. 135° C. Example No. 135°C. minutes seconds Performance Rating CE 1 8 hours — — 0.55 193 28.5 CE1 8 hours 12 (TMPTGE) 1 hour 0.49 95 47.4 CE 1 8 hours 12 (TMPTGE) 2hours 0.48 98 48.9 CE 1 8 hours 12 (TMPTGE) 3 hours 0.48 99 48.5 CE 2 8hours — — 0.50 149 33.6 CE 2 8 hours 15 (TMPTGE) 1 hour 0.44 74 59.5 CE2 8 hours 15 (TMPTGE) 2 hours 0.43 74 58.1 CE 2 8 hours 15 (TMPTGE) 3hours 0.42 75 56.0

[0157] TABLE 4 ΔOD@ 15 T ½ Performance % Loss of Example No. Treatmentminutes seconds Rating Coating 12 (TMPTGE) None 0.59 135 43.7 N/A HC0.56 140 40.0 0 HC & AR 0.59 135 43.7 5-15% 13 (PEG900) None 0.40 7950.6 N/A HC 0.39 89 43.8 <5% HC & AR 0.54 126 42.9 15-35% 14 (PCLD) None0.56 119 47.1 N/A HC 0.52 132 39.4 0 HC & AR 0.55 121 45.5 <5% CE 1 None0.59 173 34.1 N/A HC 0.56 190 29.5 0 HC & AR 0.60 178 33.7 <5%

[0158] TABLE 5 ΔOD@ 15 T ½ Performance % Loss of Example No. Treatmentminutes seconds Rating Coating 15 (TMPTGE) None 0.48 92 52.2 N/A HC 0.4695 48.4 0 HC & AR 0.48 87 55.2 <5% 16 (PEG900) None 0.40 82 48.8 N/A HC0.39 88 44.3 <5% HC & AR 0.40 80 50.0 5-35% 17 (PCLD) None 0.44 80 55.0N/A HC 0.42 91 46.2 0 HC & AR 0.44 79 55.7 0 CE 2 None 0.52 137 38.0 N/AHC 0.50 141 35.5 0 HC & AR 0.53 136 39.0 <5%

[0159] TABLE 6 Imbibition Time ΔOD@ T ½ Performance Example No. (hours)15 minutes seconds Rating 15 (TMPTGE) 4 0.55 141 39.0 8 0.56 200 28.0 17(PCLD) 4 0.53 139 38.1 8 0.58 143 40.6 18 (TMPTGE & 4 0.54 128 42.2PCLD) 8 0.59 148 39.9 CE 2 4 0.48 207 23.2 8 0.53 226 23.5

[0160] TABLE 7 ΔOD@30 ΔOD@15 T ½ Performance Example No. seconds minutesseconds Rating 19 (PEG(DGE)) 0.15 0.46 162 28.4 CE 3 0.03 0.26 1032 2.520 (PEG(DGE)) 0.12 0.40 206 19.4 CE 4 0.03 0.22 1496 1.5 21 (PCLD) 0.240.61 121 50.4 22 (PEG-900) 0.13 0.41 221 18.6 CE 5 0.07 0.43 804 5.3 23(PCLD) 0.20 0.55 147 37.4 24 (PEG-900) 0.08 0.28 312 9.0 CE 6 0.050.33 >904 <3.7

[0161] The results of Table 1 show that the photochromic lenses preparedusing the solutions of Examples 1-3 and 4-10 faded faster than thephotochromic lenses prepared using the solutions of Comparative Examples1 and 2, respectively. The Performance Rating for each of the Exampletreated lenses was higher than that of the lenses treated with theComparative Examples. Also, when the imbibition time was extended from 7to 8 hours for lenses treated with the solutions of Examples 2 and 5,the performance rating increased.

[0162] The results of Table 2 show that the kinetic enhancing additivecould be imbibed separately (Example 11) in a 3 hour first step followedby a second imbibition of photochromic compounds (CE 1) or a combinationof kinetic enhancing additive and photochromic compounds (Example 12)and result in a higher performance rating than if only photochromiccompounds are imbibed (CE 1). Imbibition of kinetic enhancing additivesin both steps resulted in a higher Performance Rating, 45.2, than whenimbibed in either the first step, 37.3, or the second step, 40.8.

[0163] The results of Table 3 show that when the kinetic enhancingadditive is used in a second imbibition step of from 1 to 3 hours animprovement in the Performance Rating over a single imbibition stepwithout kinetic enhancing additives is obtained.

[0164] Tables 4 and 5 demonstrate the effects of subsequent coatingsapplied to the lenses that have been imbibed with 2 differentphotochromic formulations, respectively, and 3 different kineticenhancing additives. The imbibed lenses were coated only with HI-GARD®1030 solution or HI-GARD 1030® solution and an antireflective coating byReflection Free, a divison of Essilor of America, with the commerciallyavailable antireflective (AR) coating sold as Relection Free® Plus. Thiscoating is a vacuum deposited AR coating. In each case a lens having notreatment was used for comparison. The thickness of the cured hardcoat(HC) was about 2 microns.

[0165] In Table 4, the Performance Rating decreased somewhat with theadditional coatings except for the HC & AR coated lenses imbibed withExample 12. The percent loss of coating of the lenses imbibed withExample 14 was unexpectedly equivalent to Comparative Example 1. Thepercent loss of coating for the lenses imbibed with Example 12 was lessthan that of those imbibed with Example 13.

[0166] In Table 5, the Performance Rating for the lenses imbibed with adifferent photochromic formulation than those in Table 4, showed adecrease for the hardcoated lenses and an increase for the hardcoatedand antireflection coated lenses. The percent loss of coating for thelenses imbibed with Example 17 was unexpectedly better than thoseimbibed with Comparative Example 2. The percent loss results for lensesimbibed with Example 15 were equivalent to the lenses imbibed withComparative Example 2 and the results of lenses imbibed with Example 16were somewhat worse than Comparative Example 2.

[0167] Table 6 shows the effect of combining an epoxy-containing kineticenhancing additive (TMPTGE) with an organic polyol (PCLD) in Example 18as compared to the individual KEA's or CE2 with no KEA, each imbibed 4or 8 hours. The Performance Rating for Example 15 decreased when thetime for imbibition was extended from 4 to 8 hours whereas there was anincrease in the 8 hour Performance Rating as compared to the 4 hourPerformance Rating of Example 17. The 4 hour Performance Rating for thecombination of KEA's in Example 18 (5% TMPTGE and 5% PCLD) unexpectedlydemonstrated synergy by having a higher Performance Rating, i.e., 42.2,than either of the individual components tested at an equivalentconcentration, i.e., Example 15 (10% TMPTGE) having a Performance Ratingof 39.0 and Example 17 (10% PCLD) having a Performance Rating of 38.1.The 8 hour Performance Rating results for Example 18 did not demonstratesynergy. Each of Example 15, 17 and 18 had a higher Performance Ratingthat CE-2 without KEA.

[0168] The results of Table 7 show that all of the photochromic lensesthat were prepared using photochromic imbibition solutions of thepresent invention in Examples 19-24, got darker after 30 seconds and 15minutes and faded faster than the photochromic lenses prepared usingComparative Examples 3-6 in the Photochromic Performance Test. ThePerformance Rating for each of the Example lenses was higher than thatof the Comparative Examples.

[0169] The present invention has been described with reference tospecific details of particular embodiments thereof. It is not intendedthat such details be regarded as limitations upon the scope of theinvention except insofar as to the extent that they are included in theaccompanying claims.

We claim:
 1. A removable imbibition composition comprising: (a) aphotochromic performance improving amount of kinetic enhancingadditive(s) comprising polyols or a mixture of polyols andepoxy-containing compounds; and (b) photochromic compound(s), whereinupon the application of the composition to the surface of an organicpolymeric article, the kinetic enhancing additive(s) and photochromiccompound(s) are transferred into the polymeric article and the residualimbibition coating(s) formed from the composition(s) is removed from thepolymeric article.
 2. The composition of claim 1 further comprising atleast one of ultraviolet light absorber(s), antioxidant(s), rheologycontrol agent(s), or leveling agent(s).
 3. The composition of claim 1further comprising a carrier of solvent(s), polymeric resin(s), or amixture thereof, provided said polymeric resin is different from thekinetic enhancing additive.
 4. The composition of claim 1 wherein thekinetic enhancing additive is present in an amount of from 0.1 to 99.9weight percent, based on the total weight of the composition.
 5. Thecomposition of claim 1 wherein the amount of kinetic enhancing additiveadded is an amount that results in at least a 10 percent improvement inthe Photochromic Performance Test when compared to a similar compositionfor the imbibition process without said kinetic enhancing additive. 6.The composition of claim 1 wherein the polyol(s) is polyester polyols,polyether polyols, amide-containing polyols, polyhydric polyvinylalcohols or a mixture thereof.
 7. The composition of claim 6 wherein thekinetic enhancing additive is polycaprolactone diol, poly(ethyleneglycol), hexane diol, polytetrahydrofuran diol, or a mixture thereof. 8.The composition of claim 6 wherein the polyester polyol is representedby the following formula: R₆—(X—(C(O)(—CR₇R₈)_(h)—CHR₉'O)_(t)—H)_(y)wherein: X is —O— or —NR₁₀—; R₁₀ is hydrogen or C₁-C₁₂ alkyl; R₆ is anorganic radical derived from an initiator; R₇, R₈ and R₉ are eachselected independently from hydrogen, C₁ -C₁₂ alkyl, C₅-C₆ cycloalkyl,C₁-C₆ alkoxy, benzyl or phenyl, provided that at least h+2 of the totalnumber of R₇, R₈ and R₉ are hydrogen; h is an integer from 1 to 6; t isan integer from 1 to 100; and y is an integer equal to from 2 to
 6. 9.The composition of claim 1 wherein the epoxy-containing compound(s) isrepresented by graphic formulae I, II, III or a mixture thereof:

wherein (i) R₁ is hydrogen or C₁-C₃ alkyl; (ii) n is the integer one,two, three or four; when n is one, A is C₂-C₂₀ alkyl, substituted C₂-C₂₀alkyl, C₃-C₂₀ cycloalkyl, substituted C₃-C₂₀ cycloalkyl; theunsubstituted or substituted aryl groups, phenyl and naphthyl;aryl(C₁-C₃)alkyl, substituted aryl(C₁-C₃)alkyl, acryloxy, methacryloxy;the group —C(O)Y, wherein Y is C₂-C₂₀ alkyl, C₁-C₆ alkoxy or aryl; orthe group —R—(OR)_(m)—OH or —(OR)_(m)—OH, wherein R is C₂-C₄ alkyleneand m is an integer from 1 to 20; said alkyl and cycloalkyl substituentsbeing carboxy, hydroxy or C₁-C₃ alkoxy, said aryl and aryl(C₁ -C₃)alkylsubstituents being carboxy, hydroxy, C₁-C₃ alkoxy or C₁-C₃ alkyl; orwhen n is from two to four, A is C₂-C₂₀ alkylene, substituted C₂-C₂₀alkylene, C₃-C₂₀ cycloalkylene, substituted C₃-C₂₀ cycloalkylene; theunsubstituted or substituted arylene groups, phenylene and naphthylene;aryl(C₁ -C₃)alkylene, substituted aryl(C₁ -C₃)alkylene; the group—C(O)Z(O)C— wherein Z is C₂-C₂₀ alkylene or arylene; the group—R—(OR)_(m)— or —(OR)_(m)—, wherein R and m are the same as definedhereinbefore; phthaloyl, isophthathoyl, terephthaloyl;hydroxyl-substituted phthaloyl, hydroxy-substituted isophthaloyl,hydroxy-substituted terephthaloyl; or a group represented by thefollowing graphic formula:

wherein R₂ and R₃ are each C₁-C₄ alkyl, chlorine or bromine; p and q areeach an integer from 0 to 4;

represents a divalent benzene group or a divalent cyclohexane group; Gis —O—, —S—, —S(O₂)—, —C(O)—, —CH₂—, —CH═CH—,—C(CH₃)₂—, —C(CH₃)(C₆H₅)—,—(C₆H₄)— or

when

is the divalent benzene group; or G is —O—, —S—, —CH₂—, or —C(CH₃)₂—,when

is the divalent cyclohexane group; said alkylene and cycloalkylenesubstituents being carboxy, hydroxy or C₁ -C₃ alkoxy; said arylene andaryl(C₁-C₃)alkylene substituents being carboxy, hydroxy, C₁-C₃ alkoxy orC₁-C₃ alkyl; and (iii) B is C₂-C₂₀ alkyl, substituted C₂-C₂₀ alkyl,C₃-C₂₀ cycloalkyl, substituted C₃-C₂₀ cycloalkyl; the unsubstituted orsubstituted aryl groups, phenyl and naphthyl; aryl(C₁-C₃)alkyl orsubstituted aryl(C₁-C₃)alkyl; said alkyl and cycloalkyl substituentsbeing carboxy, hydroxy or C₁-C₃ alkoxy, said aryl and aryl(C₁-C₃)alkylsubstituents being carboxy, hydroxy, C₁-C₃ alkoxy or C₁-C₃ alkyl. 10.The composition of claim 9 wherein R₁ is hydrogen; A is C₂-C₁₀ alkyl,phenyl, —R—(OR)_(m)—OH or —(OR)_(m)—OH, wherein R is C₂-C₄ alkylene andm is an integer from 1 to 20, when n is one; or when n is from two tofour, A is selected from C₂-C₁₀ alkylene, phenylene, —R—(OR)_(m)— or—(OR)_(m)—, wherein R and m are the same as defined hereinbefore; orphthaloyl; B is selected from C₂-C₁₀ alkyl, phenyl orphenyl(C₁-C₃)alkyl.
 11. The composition of claim 1 wherein theepoxy-containing compound is ethylene glycol glycidyl ether, propyleneglycol glycidyl ether, glycerol polyglycidyl ether, diglycerolpolyglycidyl ether, glycerol propoxylate triglycidyl ether,trimethylolpropane triglycidyl ether, sorbitol polyglycidyl ether, butylglycidyl ether, phenyl glycidyl ether, poly(ethylene glycol)diglycidylether, poly(propylene glycol)diglycidyl ether, neopentyl glycoldiglycidyl ether, N,N-diglycidyl-4-glycidyloxyaniline, glycidylphthalimide, N,N′-diglycidyltoluidine, 1,6-hexane diol diglycidyl ether,diglycidyl 1,2-cyclohexanedicarboxylate, bisphenol A or hydrogenatedbisphenol A propylene oxide adduct, diglycidyl ester of terephthalicacid, diglycidyl 1,2,3,6-tetrahydrophthalate, spiroglycoldiglycidylether, hydroquinone diglycidyl ether or a mixture thereof.
 12. Thecomposition of claim 11 wherein the epoxy-containing compound ispolyethylene glycol diglycidyl ether, trimethylol propane triglycidylether, N,N-diglycidyl-4-glycidyloxyaniline,diglycidyl-1,2,3,6-tetrahydrophthalate, glycerol propoxylate triglycidylether, diglycidyl-1,2-cyclohexane dicarboxylate or a mixture thereof.13. The composition of claim 1 wherein the kinetic enhancing additive isa mixture of trimethylolpropane triglycidylether and polycaprolactonediol.
 14. The composition of claim 1 wherein the photochromiccompound(s) have at least one activated absorption maxima within therange of 400 and 700 nanometers.
 15. The composition of claim 14 whereinthe photochromic compound(s) are selected from naphthopyrans,benzopyrans, indenonaphthopyrans, quinopyrans, phenanthropyrans,oxazines, metal dithizonates, fulgides, fulgimides or mixtures thereof.16. The composition of claim 3 wherein the carrier is water, benzene,toluene, methyl ethyl ketone, acetone, ethanol, tetrahydrofurfurylalcohol, n-methyl pyrrolidone, 2-ethoxyethyl ether, 2-methoxyethylether, xylene, cyclohexane, 3-methyl cyclohexanone, ethyl acetate,tetrahydrofuran, methanol, methyl propionate, ethylene glycol,hydroxy(C₁-C₃)alkyl cellulose, poly(vinyl pyrrolidone), polyvinylchloride, polyvinyl acetate, polyvinyl butyral, polyvinyl propionate,cellulose acetate butyrate or a mixture thereof.
 17. A process forimparting photochromism to an organic polymeric host material comprisingtransferring a photochromic amount of photochromic compound(s) and aphotochromic performance improving amount of kinetic enhancingadditive(s) comprising polyol(s), epoxy-containing compounds or amixture of polyols and epoxy-containing compounds into said organicpolymeric host material.
 18. The process of claim 17 wherein thetransferring of photochromic compounds and kinetic enhancing additivesis done from a carrier of solvent, polymeric resin or a mixture thereof,provided said polymeric resin is different from the kinetic enhancingadditive.
 19. The process of claim 18 further comprising removingcarrier residual from the surface of the organic polymeric host.
 20. Theprocess of claim 17 wherein the transferring of a photochromic amount ofphotochromic compound(s) and a photochromic performance improving amountof kinetic enhancing additive(s) is accomplished by a transferring orderstep selected from the group consisting of: (a) transferring kineticenhancing additive(s) prior to transferring photochromic compound(s);(b) transferring photochromic compound(s) prior to transferringkinetic-enhancing additive(s); and (c) transferring kinetic enhancingadditive(s) and photochromic compound(s) together.
 21. The process ofclaim 17 wherein the transferring of a photochromic amount ofphotochromic compound(s) and a photochromic performance improving amountof kinetic enhancing additive(s) is accomplished by a transferring orderstep selected from the group consisting of: (a) transferring a portionof the photochromic performance improving amount of kinetic enhancingadditive prior to transferring the photochromic compound and theremainder of the photochromic performance improving amount of kineticenhancing additive; (b) transferring a portion of the photochromicamount of photochromic compound prior to transferring the kineticenhancing additive and the remainder of the photochromic amount ofphotochromic compound; and (c) transferring a portion of thephotochromic performance improving amount of kinetic enhancing additiveand a portion of the photochromic amount of photochromic compound priorto transferring the remainder of each.
 22. The process of claim 17wherein the transferring of photochromic compounds and kinetic enhancingadditives is done with at least one of ultraviolet light absorber(s),ultraviolet light stabilizer(s), antioxidant(s), rheology controlagent(s), or leveling agent(s).
 23. The process of claim 17 wherein thepolyol(s) is selected from polyester polyols, polyether polyols,amide-containing polyols, polyhydric polyvinyl alcohols or a mixturethereof.
 24. The process of claim 23 wherein the kinetic enhancingadditive is selected from polycaprolactone diol, poly(ethylene glycol),hexane diol, polytetrahydrofuran diol, or a mixture thereof.
 25. Theprocess of claim 17 wherein the mixture of polyols and epoxy-containingcompounds is in a weight proportion of from 1:99 to 99:1.
 26. Theprocess of claim 25 wherein the polyol is polycaprolactone diol and theepoxy-containing compound is trimethylolpropane triglycidyl ether. 27.The process of claim 17 wherein the epoxy-containing compound(s) isrepresented by graphic formulae I, II, III or a mixture thereof:

wherein (i) R₁ is hydrogen or C₁-C₃ alkyl; (ii) n is the integer one,two, three or four; when n is one, A is C₂-C₂₀ alkyl, substituted C₂-C₂₀alkyl, C₃-C₂₀ cycloalkyl, substituted C₃-C₂₀ cycloalkyl; theunsubstituted or substituted aryl groups, phenyl and naphthyl;aryl(C₁-C₃)alkyl, substituted aryl(C₁-C₃)alkyl, acryloxy, methacryloxy;the group —C(O)Y, wherein Y is C₂-C₂₀ alkyl, C₁-C₆ alkoxy or aryl; orthe group —R—(OR)_(m)—OH or —(OR)_(m)—OH, wherein R is C₂-C₄ alkyleneand m is an integer from 1 to 20; said alkyl and cycloalkyl substituentsbeing carboxy, hydroxy or C₁-C₃ alkoxy, said aryl and aryl(C₁-C₃)alkylsubstituents being carboxy, hydroxy, C₁-C₃ alkoxy or C₁-C₃ alkyl; orwhen n is from two to four, A is C₂-C₂₀ alkylene, substituted C₂-C₂₀alkylene, C₃-C₂₀ cycloalkylene, substituted C₃-C₂₀ cycloalkylene; theunsubstituted or substituted arylene groups, phenylene and naphthylene;aryl(C₁-C₃)alkylene, substituted aryl(C₁-C₃)alkylene; the group—C(O)Z(O)C— wherein Z is C₂-C₂₀ alkylene or arylene; the group—R—(OR)_(m)— or —(OR)_(m)—, wherein R and m are the same as definedhereinbefore; phthaloyl, isophthathoyl, terephthaloyl;hydroxyl-substituted phthaloyl, hydroxy-substituted isophthaloyl,hydroxy-substituted terephthaloyl; or a group represented by thefollowing graphic formula:

wherein R₂ and R₃ are each C₁-C₄ alkyl, chlorine or bromine; p and q areeach an integer from 0 to 4;

represents a divalent benzene group or a divalent cyclohexane group; Gis —O—, —S—, —S(O₂)—, —C(O)—, —CH₂—, —CH═CH—,—C(CH₃)₂—, —C(CH₃)(C₆H₅)—,—(C₆H₄)— or

when

is the divalent benzene group; or G is —O—, —S—, —CH₂—, or —C(CH₃)₂—,when

is the divalent cyclohexane group; said alkylene and cycloalkylenesubstituents being carboxy, hydroxy or C₁-C₃ alkoxy; said arylene andaryl(C₁-C₃)alkylene substituents being carboxy, hydroxy, C₁-C₃ alkoxy orC₁-C₃ alkyl; and (iii) B is C₂-C₂₀ alkyl, substituted C₂-C₂₀ alkyl,C₃-C₂₀ cycloalkyl, substituted C₃-C₂₀ cycloalkyl; the unsubstituted orsubstituted aryl groups, phenyl and naphthyl; aryl(C₁-C₃)alkyl orsubstituted aryl(C₁-C₃)alkyl; said alkyl and cycloalkyl substituentsbeing carboxy, hydroxy or C₁-C₃ alkoxy, said aryl and aryl(C₁-C₃)alkylsubstituents being carboxy, hydroxy, C₁-C₃ alkoxy or C₁-C₃ alkyl. 28.The process of claim 27 wherein the epoxy-containing compound ispolyethylene glycol diglycidyl ether, trimethylol propane triglycidylether, N,N-diglycidyl-4-glycidyloxyaniline,diglycidyl-1,2,3,6-tetrahydrophthalate, glycerol propoxylate triglycidylether, diglycidyl-1,2-cyclohexane dicarboxylate or a mixture thereof.29. The process of claim 17 wherein the photochromic compound(s) have atleast one activated absorption maxima within the range of 400 and 700nanometers.
 30. The process of claim 18 wherein the carrier is water,benzene, toluene, methyl ethyl ketone, acetone, ethanol,tetrahydrofurfuryl alcohol, n-methyl pyrrolidone, 2-ethoxyethyl ether,2-methoxyethyl ether, xylene, cyclohexane, 3-methyl cyclohexanone, ethylacetate, tetrahydrofuran, methanol, methyl propionate, ethylene glycol,hydroxy(C₁-C₃)alkyl cellulose, poly(vinyl pyrrolidone), polyvinylchloride, polyvinyl acetate, polyvinyl butyral, polyvinyl propionate,cellulose acetate butyrate or a mixture thereof.
 31. The process ofclaim 17 wherein the organic polymeric host material is selected frompoly(urea-urethane), poly(C₁-C₁₂ alkyl methacrylates), poly(oxyalkylene)dimethacrylates, poly(alkoxylated phenol methacrylates), celluloseacetate, cellulose triacetate, cellulose acetate propionate, celluloseacetate butyrate, poly(vinyl acetate), poly(vinyl alcohol), poly(vinylchloride), poly(vinylidene chloride), thermoplastic polycarbonates,polyesters, polyurethanes, polythiourethanes, poly(ethyleneterephthalate), polystyrene, poly(alpha methylstyrene),copoly(styrene-methylmethacrylate), copoly(styrene-acrylonitrile),polyvinylbutyral and polymers of polyol(allyl carbonate) monomers,polyfunctional acrylate monomers, polyfunctional methacrylate monomers,diethylene glycol dimethacrylate monomers, diisopropenyl benzenemonomers, ethoxylated bisphenol A dimethacrylate monomers, ethyleneglycol bismethacrylate monomers, poly(ethylene glycol) bismethacrylatemonomers, ethoxylated phenol methacrylate monomers, alkoxylatedpolyhydric alcohol acrylate monomers, diallylidene pentaerythritolmonomers, urethane acrylate monomers, vinylbenzene monomers, styrenemonomers and mixtures of such monomers.
 32. A product of the process ofclaim
 17. 33. A product of the process of claim
 18. 34. A product of theprocess of claim
 19. 35. A product of the process of claim
 20. 36. Aproduct of the process of claim
 21. 37. A product of the process ofclaim 22.